Stereoselective Synthesis of Lower and Upper Rim Functionalized Tetra‑α Isomers of Calix[4]pyrroles

Hydroxyaryl alkyl ketones with functionalized alkyl chains often fail to produce the corresponding tetra-α calix[4]­pyrroles in Brönsted acid mediated condensations with pyrrole. A remarkable effect exerted by the addition of methyltrialkylammonium chloride during the acid-mediated syntheses of a s...

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Published in:Organic letters 2017-01, Vol.19 (1), p.226-229
Main Authors: Díaz-Moscoso, Alejandro, Hernández-Alonso, Daniel, Escobar, Luis, Arroyave, Frank A, Ballester, Pablo
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Language:English
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cited_by cdi_FETCH-LOGICAL-a345t-c59d6ef8f532975653065d311e6cdd7d421b4dd5fcdb3e5e42ee4c4b6e607ece3
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container_title Organic letters
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creator Díaz-Moscoso, Alejandro
Hernández-Alonso, Daniel
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Ballester, Pablo
description Hydroxyaryl alkyl ketones with functionalized alkyl chains often fail to produce the corresponding tetra-α calix[4]­pyrroles in Brönsted acid mediated condensations with pyrrole. A remarkable effect exerted by the addition of methyltrialkylammonium chloride during the acid-mediated syntheses of a series of meso-(tetrahydroxyaryl)-meso-tetraalkylcalix­[4]­pyrroles featuring alkyl terminal chloro or ester groups is reported. The ammonium salt enhances the cyclocondensation reaction and induces the almost exclusive formation of the tetra-α isomers.
doi_str_mv 10.1021/acs.orglett.6b03505
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title Stereoselective Synthesis of Lower and Upper Rim Functionalized Tetra‑α Isomers of Calix[4]pyrroles
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